Carbon Dioxide → 3-Hydroxy-2-naphthoic acid

HRID 1734291Notes

Reaction equation

HRID 1734291 reaction equation
[C:1](=[O:3])=[O:2].[CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O-:14].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>>[OH:14][C:5]1[C:6]([C:1]([OH:3])=[O:2])=[CH:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 23664630Sodium 2-naphtholate

Product 1

HCID 71043-Hydroxy-2-naphthoic acidYield 69%

Conditions

Temperature
240 °C

Procedure

A stainless steel pressure autoclave is charged with 50 parts of kerosene and heated to 240° C. It is then pressurized with 10 bar of carbon dioxide. Over the course of 8 hours, a mixture of 50 parts of sodium β-naphtholate and 32 parts of sodium carbonate are metered in as a suspension in kerosene via a metering pump, part of the kerosene being distilled off, condensed and transferred out of the reaction vessel at reduced pressure. After the usual workup, the 2-hydroxynaphthalene-3-carboxylic acid is obtained in a yield of 69% based on sodium β-naphtholate used. In addition, 20% of unreacted β-naphthol and small amounts of 2-hydroxynaphthalene-6-carboxylic acid and 2-hydroxynaphthalene-3,6-dicarboxylic acid are obtained.

Workup

  1. distillationdistilled off
  2. customcondensed

Sources & evidence

ORD record
ord-4dc2170b1dc64a2395acb9eab0af36db
Source dataset
uspto-grants-1996_07
Patent number
US05532406

Reaction notes

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